I am, for the most part, a relentless optimist. I embrace my inner Pollyanna. I regularly explore my goals with the Imagine Wild Success technique. Most people know this part of me, because I’m often the first to find the silver lining in any cloud.

Here’s something less visible but also very useful: I also use worrying productively. I plan ahead so that I can make myself a strong safety net. I go through mental fire drills so that I can figure out how to respond to various situations. I use the stoic practice of negative visualization to deal with loss before I have to deal with it.

I use pessimism in order to enable and support optimism. For example, a project pre-mortem is a great way to imagine causes of failure – and think about how you can prevent or address them.

I’m about ten months into this 5-year experiment with entrepreneurship and self-directed time. There are many ways it could fail. The good thing about framing it as an experiment is that even failure can give me valuable information. The main “real failure” is not being able to collect and make use of the insights it gives me. Here’s that and other things that could make this a waste of time:

When I write down my ghosts, they become less scary. Knowing that the potential failures have been written down, defined, and (somewhat) planned for, I can free myself up to think about the flip side: what does success look like? how do I get there?